


Sam Winchester, Matchmaker Extrodinaire.

by youwerefantastic



Category: Supernatural
Genre: M/M, POV Sam Winchester, Sick Castiel
Language: English
Status: Completed
Published: 2015-01-05
Updated: 2015-01-05
Packaged: 2018-03-05 11:19:54
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,680
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3118256
Author URL: https://archiveofourown.org/users/youwerefantastic/pseuds/youwerefantastic
Summary: <blockquote class="userstuff">
              <p>Sam Winchester's life is hard. Like, really hard. He's got an oblivious big brother, a sick ex-angel, and way too much sexual tension in the bunker.</p>
            </blockquote>





	Sam Winchester, Matchmaker Extrodinaire.

**Author's Note:**

  * For [delphoxdork](https://archiveofourown.org/users/delphoxdork/gifts).



It’s one moment that changes Sam Winchester’s life forever. One seemingly innocent interaction that completely changes the way he’s always seen his big brother. To be fair, Sam isn't exactly clueless (he's pretty sure guys don't platonically beat off to other guys, no matter what Dean's said about Harrison Ford), but ever since Dean got back for hell, he hasn't been chasing a lot of tail.

Except for Castiel- does emotionally chasing tail count? Not that Dean's outright said anything. Nope, he's probably having tea with Tumnus, for all Sam knows. But, well, this is the tipping point.

Since Cas became human, since he ended up having an extended sleepover at the bunker, he's pretty much been stealing Dean's clothes every day. As it turns out, angels don't get a special party favors bag once they check out of heaven, and with Sam himself being way too tall, Castiel has taken to appropriating Dean's wardrobe. Sure, Dean gave him a hard time about it, but beneath the rolled eyes there was a softer, more appreciative look. It had been just Sam and Dean sitting at the breakfast table the first time it happend, Sam trying to ignore his brother's disgusting habit of shoveling food into his mouth while giving Sam a play-by-play of the most recent Dr. Sexy episode, but they were both cut off with the sound of Castiel's quiet padding into the kitchen. Sam mumbled a good morning, looked back down to his paper. Dean, on the other hand, well, Dean’s jaw had dropped.  
If it wasn’t incredibly disgusting, Sam probably would’ve found it funny. Looking up from the article- sometimes it was hard to tell whether a death was a hunt or the beginning of an 100 Ways to Die episode- Sam made note of Cas. Bed head, like always. Blue eyes exhausted, typical of pre-coffee angels. Metallica shirt, not so usual. At first, he wasn’t really sure what had caused Dean’s reaction, but his always smooth, consistently classy brother had begun to splutter.  
“Uh, um, Cas, you’re uh, you’re wearing my shirt,” he mumbled, his cheeks turning pink. “You, you, uh, you’re looking nice.”  
“Thank you,” Castiel yawns, “I appreciate your generosity. Is there any coffee yes?”  
Sam expects Dean to respond, but as the seconds tick by, it becomes apparent that his brother has no intention of doing so. Glancing up from the rather gory account of a beheading, he sees that Dean’s eyes are fixed on the floor.  
And that’s when it hits him.  
Big Bad Hunter is in love with his fallen angel. God, Chuck could’ve gotten a movie deal with this one .At least a low budget porno.

 

First things first: planting the idea in Dean’s head. Now, it’s not that the sexual tension hasn’t reached awkward, noticeable levels, but Sam’s smart enough to realize that if the two idiots haven’t done something about it in the past five years, subtle nudging isn’t going to work. Somehow, the casual brushing of fingers, the gawking when one is shirtless, and the fascination with one another’s mouths hasn’t helped fire any neurons, and Sam figures if he waits for the two morons to figure it out, they’ll both be too old to get it up by the time they figure out they want to. So, he’s taking matters into his own hands and playing matchmaker.

Unfortunately, the job is a little bit more difficult than locking the two in a motel room until the work their shit out; years of special John Winchester training had Dean kicking down the door in moments. Sam’s done some thinking- 5 years of thinking, ever since it became obvious how middle-school-girl-with-a-crush Dean was for the angel- and had figured maybe Dean had just never thought about it. Maybe, the lack of action was due to his big brother’s complete inability to let the macho façade slip for more than five seconds and his lack of education about anything other than hetero relationships. Sam, at least, had some experience; he’d gotten up to a bit in college, after all. Dean, however, had only been raised with the no nonsense, boys like girls, real men don’t cry bullshit that had been handed to him along with his first shotgun. Charlie had widened his circles a bit, but Sam had a sneaking suspicion that his big brother had never made the link between popping a boner when Cas was in the room to actually being attracted to him. Much to Sam’s chagrin, it’s pretty impossible to have a sit down conversation with his brother about anything other than the latest hunt, so he’s resorted to more sneaky plans: educating Dean on the wonders of human sexuality with food allegories. And so that’s how Sam found himself sitting across from Dean at the diner, earnestly trying to explain how a mozzarella stick can be asexual. 

“It just doesn’t like to get involved with the others,” he was trying to explain, dangling the offending food in front of Dean, who was watching him with the quiet amusement of an indulgent doctor in the mental ward. “It can be still eaten with other foods if it wants, but it can be served by itself happily.”

“That’s great, Sammy,” Dean dismisses, picking up the menu again. “Please don’t tell me you’re going all Becky on the condiments next.”

“This mozzarella stick is what one would call asexual- Dean, Dean, are you paying attention?”

“Of course I am,” Dean rolls his eyes as he runs a hand thorugh his hair, looking out the window.

“Always have time for you.” Sam sighs. Big brothers are doofuses.

“The next one we should talk about is lettuce-“

“No, no, imagining the mozzarella sticks fucking the tomato sauce was bad enough—“

“Dean!” Sam whines exasperatedly, “the point was that the mozzarella stick wasn’t sexually attracted to anything, but the whipped cream can intermingle-“

“Intermingle? Sam, what the hell are you trying to do right now?” Dean hisses, eying the waiter sauntering by the table. And wow, if Dean can’t connect the fact that he’s checking out a guy’s ass as Sam’s trying to have a discussion on sexualities, then there’s really no hope. 

“Whipped cream,” Sam keeps going, because if there’s one thing he’s learned from his father, it’s that pure stubbornness can beat almost anyone, “Is a vital part of lots of breakfast dishes. It’s happy on top of hot chocolate and on pancakes, and pretty much tastes good on anything. You could say that the whipped cream is pansexual.”

The waiter’s walking by them again- this time facing front, limiting Dean’s ability to ogle him- and Sam sees it: the guy’s got dark hair and blue eyes, just like a certain ex-angel they both know. He gives Sam a weird glance as he passes, and Dean smirks.

“And is there a straight condiment, too?” he teases, stretching his arm over the red booth’s back. “Or is the salt gay for the pepper?”

“You’re not just gay for someone!” Sam sighs, “There’s also bisexuality, like how someone can want both ketchup and mustard on his hot dog.”

“Ha, wieners.”

Wow. Okay, that’s it. Sam’s done. Officially resigning from matchmaking. Just, one last try, right?

“Bisexuality is when—“

“I know what bisexuality is, Sam,” Dean huffs, rolling his eyes as he starts shoving the fries into his mouth. “Do I look like an idiot?”

Oh. Oh. That’s something then, huh?

Everything comes to a head that night. It’s been a tough week- human angels keep getting themselves into messes, and it’s quickly become the Winchesters’ job to get them back on their feet. So, yeah. Maybe Sam approaches the situation without a lot of kindness or empathy. So sue him. It’s just really tough to take a fully grown, millennia-old man seriously when he says something like this.

“I’ve been noticing the symptoms for roughly a week now,” Castiel is saying, seated firmly on an old armchair but leaning forwards with his hands on his lap. Glancing earnestly up at Dean, big blue eyes glassy with fever, he continues. “And I’ve come to the conclusion that I’m dying.”

Sam, of course, immediately starts laughing. Not as a mean thing, of course not, it’s just, well, Castiel needs some adjusting to humanity- like learning not to put plastic in the oven and recognizing that a common cold isn’t cancer. Immediately, Dean shoots him a glare, and shushes him.

“What do you mean, Cas?” he’s asking, sitting so close to the edge of the chair that Sam’s half afraid he’ll fall off. “Are you okay?”

“I seem to have developed a persistent cough as well as a jogging nose,” he earnestly explains.

“Runny nose,” Dean quickly corrects, a small, secretive smile developing on his face. “You’ve got a runny nose. Have you tried taking medicine?”

Castiel shakes his head mournfully, his face looking positively sorrowful.   
“Would that be of use?” he asks, gravelly voice sounding confused. “I was not aware that simple pharmaceuticals would be effective for such dire conditions.”

And, yeah, Sam’s definitely smirking now.

“Yup,” he explains, “medicines can treat things like a fever or congestion. I’m sure Dean wouldn’t mind picking up some Dayquil or something next time he’s at the store.” Dean’s nodding eagerly, already huge eyes gone even wider at the prospect of Castiel’s eminent death.  
“I don’t want to die.”  
“I guarantee you, Cas, you’re not gonna die,” Dean’s soothing, reaching an arm out to stroke Castiel’s shoulder. “Me and Sam, we’ll pull you through this, okay?”

“Look, Cas,” Sam starts, “It’s probably just a cold. If you take some medicine for a day or two, it’ll fade away. Your immune system just needs time to fight it.”

Dean’s shaking his head though, like Sam’s spitting lies just to spite Castiel’s health.   
“If you think it’s serious, me and Sam are going to treat it seriously. Now, let’s start with the medicine, and I’ll check you out-“ a violent blush blooms over Dean’s face, turning his cheeks, his ears, his neck a brilliant pink- “Sorry, I’ll, ah, check you over for symptoms.”  
“Well that settles it then,” Sam nods. “Dean will be your nurse.”

“This is not a time for joking, Sam,” Castiel scolds, “I could be very sick, you don’t—“ Thankfully, the tirade is cut off early by a vicious waves of coughing, and Sam hurriedly excused himself to give the two some alone time. Perfect timing: Dean had just slipped to the floor in front of Castiel’s chair to take his ex-angel’s temperature. 

 

For the next few days, it’s absolutely endless. Dean seems to have found his life’s calling as nurse to Castiel. Now, in theory, Sam’s meant to be the more cuddly, more sappy of the two; that’s certainly what Becky and the rest of the crazy fangirls seemed to think. However, Dean is totally a mother hen.

While Dean might claim to loathe chick flick conversations, Sam highly suspects that’s because he’d rather show his, ah, definitely only platonic affection. Every six hours, Sam watches Dean pick up the medicine bottle from its new home on the kitchen counter. Every six hours, Sam watches Dean examine the fine print on the side, carefully re-reading the directions and side effects until he’s convinced himself that it’s safe enough for Castiel to take. Then, he calls for Castiel, who slowly mopes into the room with a blanket- the soft one from Dean’s bed, Sam notes- wrapped around his shoulders. They’ll exchange about 30 seconds of quiet bickering as Dean tries to convince Castiel he is not about to die and that the cherry taste of the medicine is not toxic. Then, Dean will pour the invalid a glass of water to down it, and Castiel will grudgingly swallow.  
Over the next few days though, disaster strikes. Castiel begins to get better. In theory, this is a great thing, but in reality, half of Sam is guessing that as soon as he’s back to good health, the odds of Dean finally facing his pretty obviously requited feelings will plummet.  
Which means it’s time to pull out the big guns.  
It’s pretty easy to corner Cas; the guy hasn’t really left his place snuggled on the couch cushions except for the bathroom and Dean’s medicine routine. His face is pale, and the bags beneath his glassy eyes are gigantic. Frankly, he looks a little bit awful. Nonetheless, he kindly puts the book he’s reading aside- some Vonnegut classic probably stolen from Dean’s shelves- and turns to face Sam.  
“Good evening,” he says, the cough making his voice sound even deeper.  
“Hey Cas, I was just wondering how you’ve been feeling lately,” he tries to ask sincerely, breaking out the patented puppy eyes. “Any improvement?”  
“I believe the medicine Dean prescribed has been working well.” He’s given a weak smile, but more than anything Castiel just looks exhausted.  
“Yeah? That’s great Cas, can’t wait to have you back on your feet! There's just, uh,” okay, Sam, it’s game time, “There’s one more thing that I’ve heard might help you feel better.”  
“What would that be?”  
“Well, uh, I don’t want you to think it’s too silly…” he trails off, hoping that Cas will bite the bait.  
“Sam,” Castiel smiles, shifting beneath the blanket, “I assure you, I will approach your idea with an open mind.”  
“Are you sure? It sounds kind of weird, but it really does help, and I don’t want you to feel obliged or anything.” He feels bad lying to his friend, but hey, it’s for the greater good. Five years from now, Sam’s sure, Cas and Dean will be thanking him.  
“Sam, please, tell me your remedy.” Castiel’s sitting up a little bit more in his makeshift bed.  
“Cuddling. In bed. With someone you care about. It sounds weird at first, but—“ he’s cut off from his staccato as Castiel immediately replies.  
“That sounds pleasurable; I will suggest it to Dean.”  
“Are you sure? I don’t want you to feel obliged or anything just because I suggested it.”  
“No, I am very interested in this tactic. Thank you.”  
Sam pulls the blankets up a bit further around the ex-angel then awkwardly pets Castiel’s hair. He gives a last smile before standing up, mentally cheering at his victory. Castiel head tilts, and he soon falls back asleep.

Sam overhears the conversation that night, during the 11:00 medicine routine. He’s sitting in the next room, but the walls just aren’t that thick, and the doors are open, so it’s pretty easy to tell what’s going on. Besides, it’s not as if Dean’s ever been big on keeping secrets, unless it’s about demonic   
“Sam had an interesting idea for us to try today,” Castiel brings it up first after hesitantly cutting off Dean’s update on Dr. Sexy’s threesome. Thank God the conversation’s turning, Sam thinks; he was just about ready to jump off of a clip. “I believe it may be helpful.”  
“Yeah?” Sam can hear Dean say. “I’m up for anything. What did he suggest?”  
“Cuddling in bed with a loved one,” Castiel repeats.  
Sam hears a muffled curse, the slam of a cabinet drawer. After a moment, Dean responds.  
“Sam said that?”   
“Yes. We should, ah,” Castiel pauses for a moment, apparently fumbling with the word, “snuggle.”  
“If you want to?” Dean sounds hesitant, and Sam’s positive that if he had x-ray vision he’d be able to see Dean’s skin heat to a light pink. “I don’t want to make you think that you’ve uh, that you have to be spending more time with me if you don’t want to, you know? Like, I don’t want to take advantage of your sickness or anything, and it’s really up to you—“  
“I want to. It would be pleasurable.”

And the next day, Sam accidentally ends up walking in on Dean giving Castiel a blow job. Sure, maybe that’s a victory, but it’s also unbelievably gross. Like, scarred forever, therapy for life, gross. But hey, Mission Matchmaking is officially a success.   
Sam: 1, World: 0


End file.
